Designing Hats for Princess Diana Was a "Nightmare" Due to an "Unusual" Feature, Per Royal Milliner

From feathered fascinators to straw boaters, hats have long played a central role in royal wardrobes. Designing hats for the Royal Family requires balancing style with tradition—and having a flair for dealing with the unexpected. But according to late milliner Frederick Fox, there was once princess who posed a particularly "unusual" challenge: Princess Diana. The style icon made headlines with her fabulously '80s hats, but behind the scenes, Fox revealed that she was notoriously difficult to design for.

In the early days of her royal career, Diana was directed to the legendary Freddie Fox by Vogue editor Anna Harvey, per the book Dianaworld: An Obsession. Author Edward White wrote that Fox—"who at one point was designing hats for eight royal women", including Queen Elizabeth—found it to be "a nightmare keeping them all apart."

The late Queen's longtime milliner, Stella McLaren—who got her start in Fox's workshop—told Marie Claire last year that Fox was a fiery character but trusted by Queen Elizabeth, who granted him a royal warrant in 1974. After Princess Diana came onto the royal scene, he designed hats for the royal "for about six years in the 1980s," per White.

Noting that Fox had to deal with "convoluted etiquette" when working with Queen Elizabeth, such as walking out of a room backwards, White wrote that it was much different to design for Diana.

"Ahead of a trip to Japan, for example, Fox spread out sketches of his designs on the carpet at Kensington Palace while he and the princess sat on the floor reviewing each of them," the author penned.

However, the milliner, who died in 2013, said that Diana had a "very difficult head to fit," with White comparing it to "a huge rugby ball." The princess's head "came to a point in the front," per Fox and was "very big at the back," with the milliner calling it "a really large head."

Despite declaring that Diana was "lost" and "totally out of her depth" (and, apparently, having a huge head), Fox called the young princess "really, really sweet."

In Dianaworld, White also described how one British designer was horrified to find Princess Diana as one of her shop's very first customers. Vivienne Westwood co-owned a London boutique with Malcom McLaren, former manager of the Sex Pistols—and with her preppy "Sloane Ranger" style, Diana was far from their target customer.

"A terrible thing happened," McLaren said, per White. "We opened the store and Diana Spencer came in; she was the first customer...I thought, 'Oh my God, we're ruined!...I've lost all credibility.'"